EP2598104B1 - Use of green coffee and probiotic for regulating skin pigmentation - Google Patents

Use of green coffee and probiotic for regulating skin pigmentation Download PDF

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Publication number
EP2598104B1
EP2598104B1 EP11738709.2A EP11738709A EP2598104B1 EP 2598104 B1 EP2598104 B1 EP 2598104B1 EP 11738709 A EP11738709 A EP 11738709A EP 2598104 B1 EP2598104 B1 EP 2598104B1
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EP
European Patent Office
Prior art keywords
skin
composition
skin pigment
accordance
coffee
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP11738709.2A
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German (de)
English (en)
French (fr)
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EP2598104A2 (en
Inventor
Karin Kraehenbuehl
Olivier Mauroux
Rachid Bel Rhlid
Angus Moodycliffe
Fabiola Dionisi
Marjorie Guitard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Societe des Produits Nestle SA
LOreal SA
Original Assignee
Societe des Produits Nestle SA
Nestle SA
LOreal SA
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Priority to EP11738709.2A priority Critical patent/EP2598104B1/en
Publication of EP2598104A2 publication Critical patent/EP2598104A2/en
Application granted granted Critical
Publication of EP2598104B1 publication Critical patent/EP2598104B1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A61K8/66—Enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9728—Fungi, e.g. yeasts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/99—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from microorganisms other than algae or fungi, e.g. protozoa or bacteria
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/88—Two- or multipart kits

Definitions

  • the present invention relates generally to the field of food supplements and/or food products for cosmetic purpose. More specifically, the present invention aims to provide a composition containing green coffee beans or an aqueous extract thereof and Lactobacillus johnsonii as an active agent for treating and/or preventing skin pigment disorders and/or skin pigment imperfections, wherein said skin pigment disorders and/or skin pigment imperfections are associated with hyperpigmentation.
  • the present invention also aims at additionally improving skin tone as well as providing a skin lightening or whitening agent.
  • Skin color is primarily determined by the amount and type of melanin, a brown pigment present in the skin. Lower amounts of melanin result in lighter skin color while higher amounts result in darker skin color. Also, hyper-pigmentation in the skin is caused by the over expression or accumulation of melanin in the skin. As a result, the pathway involved in melanin production has been the target for many inhibitors so as to reduce the levels produced.
  • One of the principal enzymes involved in the melanin pathway is tyrosinase.
  • melanin is a process under hormonal control, including the melanocyte stimulating hormone (MSH) and adrenocorticotropic hormone (ACTH) peptides that are produced from the precursor proopiomelanocortin. It is stimulated by the DNA damages that are caused by UVB-radiations as well.
  • MSH melanocyte stimulating hormone
  • ACTH adrenocorticotropic hormone
  • tyrosinase inhibitors such as hydroquinone, vitamin C, cystein, kojic acid, arbutin and glutathione among others have been proposed in topical compositions.
  • tyrosinase inhibitors such as hydroquinone, vitamin C, cystein, kojic acid, arbutin and glutathione among others have been proposed in topical compositions.
  • a variety of dermatological compositions have been suggested for improving the appearance of pigment disorders such as that observed in melasma, freckles, vitiligo, piebaldism, phenylketonuria, and the like, and/or for cosmetic purposes.
  • Topical retinoid and topical corticosteroids have been suggested as hypo-pigmenting agents, as have laser treatment and chemical peels, but these fall short of desirable responses.
  • compositions suggested the use on the skin of natural materials, which have in some cases been used for centuries in Asia or Europe to bleach skin and skin areas, or enhance the appearance of fair skin. These include the use of lemon, orange, cucumber, ginkgo, carob, rose fruit, geranium herb, cinnamon, sweet marjoram, rosemary, etc.
  • the object of the present invention is to meet these needs.
  • the present inventors could achieve this object by providing a food or food supplement composition that comprises at least an ingredient containing green coffee beans treated with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids.
  • a food or food supplement composition that comprises at least an ingredient containing green coffee beans treated with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids.
  • the invention relates to the cosmetic use of an effective amount of at least an ingredient containing green coffee portions with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids as an active agent for treating and/or preventing skin pigmentation disorders.
  • skin disorder are in particular those due to age or to environmental factors (e.g. UV), such as age-spots. It may also be skin disorders that are observed in melasma, freckles and/or age spots.
  • skin is intended to mean the skin of the face or of the body.
  • the term "effective amount”, is intended to mean an amount sufficient to obtain the expected effect.
  • the term "prevent” is intended to mean the fact of reducing the risk of occurrence of the manifestation of the disorder under consideration.
  • the present invention is also directed towards the cosmetic use of the abovementioned ingredient, as an active agent for treating and/or preventing the skin pigment imperfections.
  • the complexion becomes brighter and more homogeneous, without areas of dyschromia, or of dryness.
  • the present invention is also directed towards the cosmetic use of an effective amount of at least an ingredient containing green coffee beans according to the invention, as an active agent for whitening or lightening skin tone.
  • a use in accordance with the present invention may also comprise the use of at least an ingredient containing green coffee beans, in combination with an effective amount of at least one active agent for further improving skin hydration or skin ageing, in particular as described hereinafter.
  • the subject of the invention is a method, in particular a cosmetic method, for treating and/or preventing skin tone imperfections and the disorders associated with hyper-pigmentation, in particular aesthetic disorders, in an individual, comprising at least one step of administering, to said individual, at least an ingredient containing green coffee beans according to the invention.
  • compositions according to the present invention are orally administrable. This has the advantage of acting globally on the entire skin, in its deep layers (dermis, hypodermis), by means of a rapid and relatively non-restrictive mode of administration. Specifically, the metabolites and other active nutriments are in particular distributed within the dermal matrix by means of the bloodstream. Oral administration also has the advantage of a rapid and relatively non-restrictive mode of administration.
  • the present invention provides the use of green coffee beans with a Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids.
  • Chlorogenic acids are a family of esters formed between trans-cinnamic acids and quinic acid. Chlorogenic acids are naturally present in coffee, mainly as mono- and di-esters of quinic acid and phenolic groups (e.g. caffeic, ferulic, coumaric, methoxycinnamic) attached to different positions.
  • phenolic groups e.g. caffeic, ferulic, coumaric, methoxycinnamic
  • the microorganism is capable of hydrolysing caffeoyl quinic acid and diesters (e.g. 3-, 4-, or 5-caffeoyl quinic acid and diesters), and/or feruloyl quinic acid and diesters (e.g. 3-, 4-, or 5-feruloyl quinic acid and diesters), to generate caffeic acid and ferulic acid, respectively.
  • caffeoyl quinic acid and diesters e.g. 3-, 4-, or 5-caffeoyl quinic acid and diesters
  • feruloyl quinic acid and diesters e.g. 3-, 4-, or 5-feruloyl quinic acid and diesters
  • composition of the invention should be formulated such that the microorganism will not ferment or react with the composition during storage. This may be achieved e.g. by formulating the composition as a dry powder, and/or by encapsulating the microrganism and/or enzyme so that the microorganisms and/or enzyme will only be released when the composition is mixed with coffee extract or during digestion.
  • a coffee extract according to the invention is an extract of green coffee beans by water or steam. Numerous methods for producing coffee extracts are known in the art.
  • a coffee bean extract can be obtained by an aqueous, aqueous- alcoholic or alcoholic extraction of coffee beans, and preferably by an extraction with the aid of methanol, ethanol or propanol.
  • the green coffee may be derived from Arabica or Robusta, or may be a blend of Arabica and Robusta.
  • the green coffee portion may be at least partially decaffeinated. This is to provide products the caffeine level of which can be modulated from caffeine-free to regular caffeine level.
  • Microorganisms capable of hydrolysing chlorogenic acid may e.g. be identified as disclosed in the examples of this application.
  • the suitable microorganism is a Lactobacillus, being L. johnsonii (CNCM I-1225).
  • the microorganism should be present in an amount sufficient for hydrolysing a substantial amount of chlorogenic acids present in the coffee extract to phenolic acids during digestion. Preferably at least 20%, such as at least 30%, at least 50%, or at least 75% of caffeoyl quinic acids (CQA) and/or feruloyl quinic acids (FQA) present in the coffee extract is hydrolysed.
  • CQA caffeoyl quinic acids
  • FQA feruloyl quinic acids
  • compositions according to the invention may be in any of the galenical forms normally available for the method of administration selected.
  • the carrier may be of diverse nature depending on the type of composition under consideration. Accordingly, the composition may be any food or pharmaceutical product, or a cosmetic product for oral application.
  • food or pharmaceutical carriers nutritional complete formula, dairy product such as milk, yogurt, cheese, fermented milks, milk-based fermented products, ice-creams, cereal-based products or fermented cereal-based products, milk-based powders, infant and baby formulas, chilled or shelf stable beverages, food products of confectionary, chocolate or cereal type, animal feed, in particular for domestic animals.
  • the chicory or extract thereof may be incorporated into any other form of food supplement or enriched food, for example food bars or compacted or non-compacted powders.
  • the powders may be diluted in water, soda, milk products or soya bean derivatives, or be incorporated into food bars.
  • the food product may also further comprise a protein source, a carbohydrate source, a lipid source, a mineral source and/or a vitamin source.
  • a protein source a carbohydrate source
  • a lipid source a mineral source and/or a vitamin source.
  • proteins, carbohydrates, lipids, minerals and/or vitamins may have several advantages. These compounds generally contribute to the taste and mouthfeel of the final product. They also provide the body with nutrients that it may need urgently when it is affected by skin disorders. They also allow formulating the product of the present invention as a complete nutritional formula, so that no additional nutrition is needed.
  • the individual ingredients may comprise any kind of edible compound.
  • Typical ingredients for food compositions, in particular drinks are well known in the art, e.g. milk, cream, coffee whiteners, and coffee creamers.
  • ingredients could also be a salad dressing or parts thereof, for example.
  • Such compounds are used by consumers to modify e.g. the aroma, appearance and texture of a composition.
  • the ingredients may be in liquid or dry form, e.g. as powders, that are dissolved and/or suspended in a drink.
  • the invention also provides a coffee beverage product, such as (a) a roast and ground coffee product, (b) a soluble coffee product, (c) a single portion coffee pad, tablet or capsule (d) a ready to drink coffee product or (e) any other suitable coffee product, comprising the coffee product as defined herein as an ingredient.
  • a coffee beverage product such as (a) a roast and ground coffee product, (b) a soluble coffee product, (c) a single portion coffee pad, tablet or capsule (d) a ready to drink coffee product or (e) any other suitable coffee product, comprising the coffee product as defined herein as an ingredient.
  • Soluble coffee or instant coffee as it is otherwise known is very well known and has been produced commercially for many decades. It is produced from roast and ground coffee in a variety of ways, all of which are well known to the person skilled in the art.
  • the present invention is particularly suitable for use as a soluble coffee product or any product, which is based on or derived from a soluble coffee product.
  • the coffee product may also be used in so-called ready-to-drink beverages.
  • ready-to-drink beverages for which the product of the present invention are suited include two-in-one beverages which comprise a coffee component together with a natural or artificial sweetener component, the components optionally being pre-diluted with a liquid such as water or milk.
  • the coffee component can comprise the coffee product described herein.
  • Three-in-one beverages which comprise coffee, a sweetener and a whitener such as milk, a liquid creamer or a solid (e.g. powdered) creamer, may comprise the coffee product described herein.
  • any beverage which comprises soluble coffee as an ingredient, may comprise the coffee product described herein.
  • the composition may further comprise further ingredient suitable for inclusion in a food composition.
  • Usual ingredients may e.g. be sugars, artificial sweeteners, emulsifiers, stabilizers, thickeners, flowing agents, colors, flavors, aromas, and the like.
  • Suitable artificial sweeteners include saccharin, cyclamates, acetosulfame, L-aspartyl based sweeteners such as aspartame, and mixtures of these.
  • Suitable emulsifiers include monoglycerides, diglycerides, lecithin, diacetyl tartaric acid esters of mono-diglycerides, emulsifying starches, and mixtures thereof.
  • Suitable stabilisers include dipotassium phosphate and sodium citrate.
  • a suitable flowing agent is sodium silica aluminate.
  • the composition comprises milk protein and/or vegetable protein.
  • the composition comprises milk fat and/or vegetable fat.
  • the product described herein can be used as an ingredient for standard brew, espresso, coffee-based beverage preparations to be used as bulk or in single beverage portion for in-home preparation.
  • the product is a nutritional supplement for oral administration it may be present in capsules, gelatin capsules, soft capsules, tablets, sugar-coated tablets, pills, pastes or pastilles, gums, or drinkable solutions or emulsions, a syrup or a gel.
  • a supplement might also include a sweetener, a stabilizer, an antioxidant, an additive, a flavoring agent and/or a colorant.
  • the formulation thereof is carried out by means of the usual methods for producing sugar-coated tablets, gel capsules, gels, hydrogels for controlled release, emulsions, tablets or capsules.
  • the adjuvant for oral compositions, in particular for dietary supplements are known to the specialist.
  • lubricants such as magnesium stearate, products for instantaneous solubilisation, gelling agents, thickeners, moisturizers, fatty and/or aqueous compounds, preservatives, texturizing, flavoring and/or coating agents, anti-oxidants and coloring materials usually used in foods.
  • composition described herein may contain, in addition, lipids, polyphenols, taurine, other probiotic microorganisms, vitamins and/or oligo-elements. If probiotics are used, they may be included in a live form, semi-active or in a desactivated form, e. g., as a lyophilized powder.
  • a kit comprising at least two parts: a) a first part comprising a coffee extract; and b) a second part comprising a microorganism and/or an enzyme capable of hydrolysing chlorogenic acids to generate phenolic acids.
  • the two parts are sold together for the preparation of a composition but are physically separated in the packing of the product.
  • the final composition to be consumed is prepared by mixing the two parts shortly before consumption. If one or both parts are in a liquid form they may be mixed directly, optionally further liquid, e.g. water or milk, may be added.
  • the two parts may also be mixed by dissolving or suspending them in a liquid, e.g. water or milk.
  • liquid When liquid is used this may be hot or cold depending on whether a hot or a cold beverage is desired. If hot liquid is used, it may preferably have a temperature which is not so high as to inactivate the microorganism and/or enzyme before ingestion of the composition.
  • the first part of the kit comprises a coffee extract.
  • the first part is in a dry form, e.g. in the form of a powder.
  • the coffee extract may e.g. be a spray dried or freeze dried green coffee extract.
  • the first part may also be in a liquid form. Liquid coffee extracts are readily available e.g. as ready-to-drink coffee beverages.
  • the first part may additionally comprise any other suitable ingredient, e.g. chicory extract, aroma additives, stabilisers, salts, and/or sweeteners.
  • the first part may be packed in any suitable way, e.g. in a sachet, bottle or can.
  • the second part comprises a microorganism and/or an enzyme capable of hydrolysing chlorogenic acids to generate phenolic acids.
  • This part may preferably be in the form of a composition to be mixed with a coffee extract as described herein, preferably in the form of a coffee whitener or coffee creamer. It may comprise any other suitable components. It may be in dry form, e.g. as a powder, or in liquid form, and may be packed in any suitable way, e.g. in a sachet, bottle or can. It should be formulated such that the microorganism and/or enzyme will not ferment or react with other ingredients during storage. This may be achieved e.g. by formulating the composition as a dry powder, and/or by encapsulating the microrganism and/or enzyme so that the microorganisms and/or enzyme will only be released when the composition is mixed with coffee extract or during digestion.
  • the at least two parts may be packed together in any suitable way. They may e.g. be packed in a combined container wherein the parts are kept physically separated during storage and mixed when the container is opened, or they may be packed in separate containers which are sold together for the preparation of a beverage.
  • the products described herein are used for treating or preventing skin pigmentation disorders or cosmetically lightening skin tone e.g. by decreasing the production of melanin.
  • green coffee beans extracts were shown to decrease in vitro the synthesis of melanin (Example 1, Figure 1 ).
  • the production of tyrosinase was also decreased but to a limited extent ( Figure 2 ), suggesting that the decrease in melanin was not due to tyrosinase inhibition but rather to mechanisms acting upstream or downstream of this enzyme.
  • the ingredients according to the present invention have further a positive effect on strengthening skin barrier and maintaining skin hydration.
  • the invention relates to the cosmetic use of an effective amount of at least one ingredient containing green coffee beans with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids for treating and/or preventing skin pigmentation disorders, in particular those due to age or environmental factors such as UV.
  • the present invention is also directed towards the cosmetic use of an effective amount of at least one ingredient containing green coffee beans with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids for whitening or lightening skin tone, which is particularly desirable for asian population.
  • a use in accordance with the present invention may also comprises the use of at least one ingredient containing green coffee beans with microorganisms capable of hydrolysing chlorogenic acids to generate phenolic acids, in combination with an effective amount of at least one active agent for improving skin hydration or skin ageing, in particular as described hereinafter.
  • the subject of the invention is a method, in particular a cosmetic method, for treating and/or preventing skin tone imperfections and/or disorders associated with hyper-pigmentation, in particular aesthetic disorders, in an individual, comprising at least one step of administering, to said individual, at least one ingredient containing green coffee beans with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids according to the invention.
  • the cosmetic treatment method of the invention is carried out by orally administering at least an effective amount of at least one ingredient containing green coffee beans with Lactobacillus johnsonii capable of hydrolysing chlorogenic acids to generate phenolic acids in accordance with the invention.
  • Oral administration comprises ingesting, in one or more intakes, an oral composition as defined above.
  • the application may comprise a single application.
  • the application is repeated, for example, 2 to 3 times a day, for one day or more, and generally for a sustained period of at least 4, or even 1 to 15, weeks.
  • an oral treatment with a composition containing green coffee beans in accordance with the invention, combined with a topical composition optionally containing another active ingredient, in particular a probiotic microorganism, or other probiotics in dead, live or semi-active form or an hydrating or anti-ageing agent could be imagined as a kit.
  • the ingredients are mixed, before they are formulated, in the order and under conditions readily determined by those skilled in the art.
  • the proportion of coffee bean extract in the composition will of course be determined as a function of the desired effect and on the mode of administration of the composition.
  • the daily doses of green coffee bean extract administered by the oral route may preferably be comprised between 0.1 and 27 g/day depending on the type of product and the caffeine content, more preferably 0.5 to 18 g/day, even more preferably 1 to 3 g/day.
  • the present inventors have found that the effectiveness of green coffee bean extracts according to the present invention is generally dose dependant and follows a dose response curve. If generally mild skin disorders or damages are to be prevented and the product will be used frequently, very small amounts will be sufficient to achieve the desired effect. If a severe skin pigment disorder is to be treated, larger amounts will be more appropriate, although also small amounts will produce an effect.
  • the composition intended for oral administration contains an extract of coffee beans in a quantity ranging from 1% to 80% by weight of the composition and preferably from 10 % to 80% by weight of the composition depending on the product form.
  • Coffee samples were diluted to 1% w/w and analyzed by RP-HPLC on a CC 250/4 Nucleosil 100-5-C18 column (Macherey-Nagel).
  • the eluent system was Millipore water, 0.1% TFA and CH 3 CN at a flow rate of 1 mL/min.
  • the method allowed the simultaneous determination of caffeoyl quinic acids (CQA), feruloyl quinic acids (FQA), di-caffeoyl quinic acids (diCQA), feruloyl quinic acid-lactones, caffeic acid (CA) and ferulic acid (FA) (absorbance at 325 nm) using external standard calibration curves. Results were expressed relative to the reference at time 0 (t0) or to the reference at the same time without bacteria.
  • B16 cells were cultured in DMEM 1g/L glucose without phenol red supplemented with 10 % foetal calf serum, in a humidified chamber at 37 °C and containing 5% CO 2 .

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EP11738709.2A 2010-07-30 2011-07-29 Use of green coffee and probiotic for regulating skin pigmentation Active EP2598104B1 (en)

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EP10171380 2010-07-30
PCT/EP2011/063059 WO2012013762A2 (en) 2010-07-30 2011-07-29 Use of green coffee and probiotic for regulating skin pigmentation
EP11738709.2A EP2598104B1 (en) 2010-07-30 2011-07-29 Use of green coffee and probiotic for regulating skin pigmentation

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EP2598104A2 EP2598104A2 (en) 2013-06-05
EP2598104B1 true EP2598104B1 (en) 2019-12-18

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EP (1) EP2598104B1 (ru)
JP (1) JP2013533280A (ru)
CN (1) CN103068359A (ru)
BR (1) BR112013002195A2 (ru)
ES (1) ES2773723T3 (ru)
MX (1) MX358237B (ru)
RU (1) RU2013108969A (ru)
WO (1) WO2012013762A2 (ru)

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JP2015140309A (ja) * 2014-01-28 2015-08-03 一丸ファルコス株式会社 カフェ酸又はカフェ酸誘導体を有効成分とするキネシン抑制剤
JP7048249B2 (ja) * 2017-10-18 2022-04-05 花王株式会社 足の皮膚常在細菌叢改善剤
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ES2773723T3 (es) 2020-07-14
EP2598104A2 (en) 2013-06-05
WO2012013762A3 (en) 2012-03-22
CN103068359A (zh) 2013-04-24
MX2013001077A (es) 2013-06-07
RU2013108969A (ru) 2014-09-10
MX358237B (es) 2018-08-10
WO2012013762A2 (en) 2012-02-02
BR112013002195A2 (pt) 2016-11-08
JP2013533280A (ja) 2013-08-22

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